Five Years a Comedian’s Assistant: What It’s Like Working for the Most Neurotic Bosses Around

Hi, I’m Stephie, and I’m a recovering assistant-aholic. For the past five-plus years, I’ve had the incredible fortune of working for a whole slew of professional funny people.

Many of my jobs were in film/TV production: as a personal assistant, production assistant, writer’s assistant, associate producer, and script supervisor, multiple times over in each capacity. But my absolute favorite gigs — the ones where I really cut my care-of-comedians teeth — were as road manager on three cross-country tours. If there’s one place to get to know a comedian (or anyone) in a profound way, it’s inside a compact rental car with a faulty GPS, desperately trying to find the highway out of Flint, Michigan.

First of All, I’m Mom

This was Surprise #1. I first thought I’d been hired to be almost invisible — to do simple stuff my bosses didn’t have time for, but without leaving any trace of my existence. Like Santa Claus, if Santa left organized filing systems and updated calendars under the tree instead of toys.

As time progressed and my bosses entrusted me with more personal responsibilities beyond easy errands, I unwittingly began to assume Mom Role. Mom thinks twelve steps ahead. She strives to make life easier for her kids, and is so on point with her mom-ness that she’s clearly the envy of all the other neighborhood moms. Or, put another way: I became my own mom.

The first time I felt vaguely maternal pangs cropped up when one boss asked me to complete an emailed Q&A as him, then fretted, “Is that totally awful?” I swiftly reassured him, “You are so stressed right now. I got this.” Even then, it reminded me of the more-than-one-occasion where my mom sent me to bed to complete dioramas I was doing a piss-poor job of hot gluing, soothing my panicked “Is this cheating?” fears with calm, “Go to sleep. I got this.”

My bosses all had terrific moms and spouses; but I learned real fast that the quickest way to legitimize my paycheck (and bolster my sense of self worth, no doubt) was to metaphorically cut the crusts of their bread. This entailed assuming the three overarching job functions of parents: (1) get kids’ shit together, (2) make kids feel safe, and (3) validate kids with praise.

On Being Benignly Neurotic

We’re ALL a little neurotic, right? Totally. I have a ritual in which I compulsively touch all the knobs on the stove before I leave the house. And I legitimately think I’m about to die every time my subway stops between stations. But, my neuroses are not my job. Comedians’ neuroses are their bread and butter and jam and Nutella.

Their brains are full! Their brains are like post-Thanksgiving tummies, 24/7. Always digesting.

Speaking of tummies, they certainly don’t need to exert brain cells fixating on food. Food is fuel, and I quickly discovered it was the easiest problem I could solve for them. Enter: Stephie!

I memorized how light one comedian liked his coffee by internalizing the color he showed me — “This medium brown, like Mark’s sweater” — which equates to pouring skim milk for exactly the length of the “Yo!” preceding “I’ll tell you what I want what I really really want” in Spice Girls’ “Wannabe.”

Another boss had a weird thing about condiments. I’d hysterically beg the poor deli cashier, “Please, sir! Plain! Nothing on it! Please!” and then rifle through the bag for ketchup, mustard and mayo packets rashly flung in there before presenting my boss his immaculately unembellished turkey on wheat.

And after traveling on the road with yet another comediboss, I discovered it was imperative to keep an overstock of Marlboro Mediums and Trident White Cool Bubble Sugarless Gum in my suitcase at all times. Nothing bad would’ve happened if I’d ran out, but I wouldn’t have been “ohmygosh, so amazing, Stephie.”

Perfect Mom’s kids never ask her to bake cookies; she just does it.

On Being Even More Neurotic Than I Initially Conceived

I hoped to alleviate the most banal of my bosses’ neuroticisms by becoming even more neurotic myself. They felt safe with me (I think/hope) because they knew I’d be neurotic about everything other than that thing that happened when they stood on line at the drugstore, the weird way people are when they do that thing they do, etc. And in day-to-day life sans assistant, comedians do not naturally feel safe.

Comedians are often:

-Insecure
-Obsessive
-Sensitive
-Anxious
-Sensitive

I said “sensitive” twice because they’re doubly more sensitive than you’d think, despite their career-required resilience. Skin exposed to the sun will get burned. Comedians are unabashedly emotionally naked; their skin is thick, but it’s sunny-side-up nonstop.

This was Surprise #2. I was a twenty-two year old pup on my first gig, and I was shocked to discover that my new bosses were hardly as confident as they seemed, despite being perpetually “on.”

At first I didn’t know how to handle it. Should I laugh at everything because everything is hilarious? Should I remain steely and straight-faced because I’m a professional and we’re working here? Should I geek out because I’m a fan? Well, none of those are right.

I once made the rookie mistake of insulting my boss. We were on a month-long tour, and I’d worked for him long enough already that he’d begun to workshop ideas with me. One night as we devoured post-show pancakes, he asked what I thought of a specific joke. I said, “It wasn’t for me?” I thought we’d reached a level of familiarity in which my feedback could be totally honest. I didn’t realize that my noncommittal shrug was on par with, “Meh.” Meh isn’t an opinion. Meh is a real lousy thing to say to someone who just mopped the floor with his I’m Doing This For You Guys! sweat. He felt hurt and depleted; I felt confused, but later as I tossed and turned on a crummy Holiday Inn mattress, I realized I completely failed him.

The stereotype that comedians ask “is this funny?” because they need approval is wrong. Their jobs are all about reactions and reviews. Making them feel safe means responding positively to their work. I needed to be “on,” too. Once I realized that I was my bosses’ test subject, and not a Yes Man Robot on the one hand, or an in-house critic on the other, I learned how to tailor my feedback to reflect not only honesty, but also sensitivity and humility.

It’s a good rule to apply to all relationships, really.

On Being the Beloved Butt of the Joke

I drove too slow. I ate too slow. I was naïve. “There there, Stephie,” was a purposefully patronizing thing they’d lay on thick with a performative pat on the head. But you know how in grade school the kid on the playground who teased you really liked you? This is similar. It’s a lot like hazing, too. Frats want to see if you can take the heat. If you can, you’re in. I was in.

At a certain point I felt like I’d accidentally received keys to an exclusive club (of which I desperately wanted to be a member, despite Groucho Marx’s sentiments), but anxiety soon trumped achievement. I privately fell into an “I’m not worthy!” Wayne and Garth tizzy, freaking out that all the funny people would discover that the emperor has no clothes and Stephie has no original jokes.

Welcome though these comics made me feel, I ultimately decided this: I wasn’t one of them. And that was a relief. They didn’t expect me to be a regular riot; they expected me to be myself.

Not all comedibosses are created equal, though; I got lucky with mine. One time I accompanied my boss to another comedian’s house. Inside sat a waifish college grad slicing the cellophane off her boss’s CDs — his stand-up special CDs. A couple hundred towered on a table beside her in precariously balanced stacks, and a box of a couple hundred more sat at her feet. Later in the car I thanked my boss: “Bless you for never making me do that.”

I went into my first job worrying it’d be tricky to eventually move on since everyone I’d meet would only see me as an assistant. What I came out realizing, however, is that the hardest thing about not being an assistant anymore is telling myself that’s no longer who I am. For so long my identity was tied up in working for talented, important people. Who am I now if I’m not the “Assistant to”? What have I done in the past five years besides worry about those dudes?

It’s tough turning that assistant’s brain off. We never really stop taking care of each other, not if we like doing it. Because when my funny bosses would tell me, in complete earnestness, “you’re indispensable” — that was the assistant equivalent of a standing-O.